Acetic Acid → HCID 59835806, compound

HRID 1916687Notes

Reaction equation

HRID 1916687 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([N:40]4[CH2:44][CH2:43][C:42](=O)[CH2:41]4)=[N:38][CH:39]=3)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.[CH3:46][CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([N:40]4[CH2:44][CH2:43][CH:42]([N:50]5[CH2:51][CH2:52][CH:47]([CH3:46])[CH2:48][CH2:49]5)[CH2:41]4)=[N:38][CH:39]=3)=[N:30][CH:31]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 693814-MethylpiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67365019HCID 67365019, compound

Product 1

HCID 59835806HCID 59835806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

48 mg (0.22 mmol) NaBH(OAc)3 and 27 μL (0.47 mmol) acetic acid are added to a solution of 100 mg (0.19 mmol, 70% purity) 1-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-pyrrolidin-3-one and 22 μL 4-methylpiperidine (0.19 mmol) in 5 mL THF. The reaction mixture is stirred overnight and combined with saturated NaHCO3 solution. The organic phase is extracted twice with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography using HPLC-MS.

Workup

  1. extractionThe organic phase is extracted twice with EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customFurther purification

Sources & evidence

ORD record
ord-02e9ac73bcd34253bed49936677944f9
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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